US4093461A - Positive working thermally stable photoresist composition, article and method of using - Google Patents
Positive working thermally stable photoresist composition, article and method of using Download PDFInfo
- Publication number
- US4093461A US4093461A US05/597,226 US59722675A US4093461A US 4093461 A US4093461 A US 4093461A US 59722675 A US59722675 A US 59722675A US 4093461 A US4093461 A US 4093461A
- Authority
- US
- United States
- Prior art keywords
- diazide
- polyamic acid
- condensation product
- support
- photoresist
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 title claims description 18
- 229920005575 poly(amic acid) Polymers 0.000 claims abstract description 28
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000007859 condensation product Substances 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 claims abstract description 7
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000011521 glass Substances 0.000 claims description 7
- 239000004642 Polyimide Substances 0.000 claims description 6
- 229920001721 polyimide Polymers 0.000 claims description 6
- 239000004065 semiconductor Substances 0.000 claims description 6
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 claims description 5
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 238000001020 plasma etching Methods 0.000 abstract description 2
- 238000000992 sputter etching Methods 0.000 abstract description 2
- 238000005468 ion implantation Methods 0.000 abstract 1
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 abstract 1
- 238000000576 coating method Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 239000012670 alkaline solution Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000007614 solvation Methods 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical compound [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salts Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 125000006160 pyromellitic dianhydride group Chemical group 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
Definitions
- the present invention relates to photoresists, and more particularly to a positive-working, thermally stable photoresist.
- Thermal stability in this context means not only that the resist does not decompose at a given temperature but that images in the resist undergo little or no dimensional changes or distortion at the given temperature.
- photoresists having stability at high temperatures, such as about 300° C and higher.
- Conventional photoresists are available with thermal stability at about 160° C, and while they are useful at temperatures up to 160° C, their thermal stability above 160° C is not sufficient for use in the high temperature processes described above.
- a negative-working photoresist is disclosed in U.S. Pat. No. 3,623,870, which is stated to have improved thermal properties. Negative-working resists are in widespread use, but nevertheless positive-working resists have inherent advantages over negative-working resists, as is well known. A positive-working, thermally stable photoresist would be highly advantageous and much prized by the workers in the art.
- the present invention fulfills this objective by providing a thermally stable photoresist composition, which comprises a light-sensitive orthoquinone diazide or orthonaphthoquinone diazide and a polyamic acid condensation product of an aromatic dianhydride and an aromatic di-primary amine.
- An improved thermally stable, supported positive-working photoresist is also provided by the invention, which comprises a base material having coated thereon the photoresist composition of the invention.
- the orthoquinone diazides and orthonaphthoquinone diazides used are known light-sensitive compounds that are water-insoluble, hydrophobic, and organic solvent soluble. Upon exposure to light, the compounds are converted into derivatives that are soluble in an aqueous alkaline solution.
- the polyamic acid reaction product used as the binder is also organic solvent soluble and is soluble in aqueous alkaline solution.
- the photoresist composition of the invention is coated on a support as a solution in an organic solvent, and the imagewise exposed photoresist is developed with an alkaline aqueous solution.
- Light-struck areas contain a mixture of polyamic acid resin and the reaction product of the orthoquinone diazide that is soluble in the aqueous alkaline developer, so that the mixture can be removed from the support during treatment with the alkaline aqueous developer.
- Areas that are not light-struck contain a mixture of polyamic acid resin and the diazide that is insoluble in the aqueous alkaline developing solution because of the hydrophobicity and insolubility of the diazide before photolysis. Hence a positive image is formed on the support corresponding to the master pattern used during imagewise exposure.
- the present invention is based on the use of a positive-working photoresist that can be coated on a support from an organic solvent and developed by an aqueous alkaline solution.
- a positive-working photoresist that can be coated on a support from an organic solvent and developed by an aqueous alkaline solution.
- the present invention is able sharply to distinguish between imagewise exposed and non-exposed areas during development and thus ensure that only light-struck areas are dissolved by solvation by the developer whereas imagewise non-exposed areas are unaffected by the developer.
- U.S. Pat. No. 3,623,870 a negative-working photoresist is disclosed having a light-sensitive dichromate and a polyamic acid binder.
- the dichromate in the light-struck areas cross-links the polyamic acid binder to form a product that is less soluble in the developer than the uncross-linked polyamic acid.
- the polyamic acid condensation product of an aromatic dianhydride and an aromatic di-primary amine is readily formed.
- a particularly suitable aromatic dianhydride is pyromellitic dianhydride.
- Suitable aromatic diamines are aromatic di-primary amines of the benzene or naphthalene series, including di-primary amino phenyl ethers.
- Such polyamic acid condensation products are known, e.g. in U.S. Pat. No. 3,179,634, and are readily converted by heat to a thermally stable polyimide that is water-insoluble, resistant to dilute acids and organic solvents and heat stable at temperatures in excess of 400° C.
- the photoresist composition of the invention is prepared by mixing the diazide with the polyamic acid condensation product in an organic solvent, such as 1-methyl-2-pyrrolidone, dimethylformamide, dimethylacetamide, and the like.
- an organic solvent such as 1-methyl-2-pyrrolidone, dimethylformamide, dimethylacetamide, and the like.
- the weight ratio of polyamic acid to diazide will be from about 1:20 to about 10:1, preferably from about 1:10 to about 5:1.
- the polyamic acid is prepared in an organic solvent, such as a solution containing from about 10 to about 20% polyamic acid, and conveniently the diazide is added to this solution.
- the quantity of solvent and its volatility are selected to obtain the specific thickness and coating quality desired in accordance with known coating techniques.
- the solution of diazide and polyamic acid in the organic solvent is coated on a suitable support by any customary procedure, as by spin coating, dipping, brushing, rolling, spraying and the like.
- the particular technique employed depends on the consistency, viscosity and solids content of the solution.
- Spin coating at 2000 to 10000 rpm for 1 to 90 seconds has been found to be acceptable and results in a uniform photoresist layer.
- the thickness of the photoresist layer on the support may range from about 0.3 to about 100 microns. When the thicker coatings are used, the time required for exposure and for developing the plate increases. For most uses, a thickness of from about 0.3 to about 8 microns, preferably 0.8 to about 4 microns, will give satisfactory results.
- thinner thicknesses are required, generally ranging from about 15 to about 100 microns, preferably from about 25 to about 50 microns.
- the support can be maintained at room temperature so as to permit evaporation of the solvent; preferably it is put in an oven at a temperature of about 80° C to accelerate the evaporation of the solvent.
- any suitable support may be used for the photoresist, such as those employed in the microelectronic and printed circuit industry.
- Such supports include glass, metallic plates, bi-mettalic and tri-metallic plates, semi-conductor wafers, finished printed circuits and the like.
- the photoresist of the invention may be imagewise exposed through a positive or negative mask, customarily a negative mask, by a suitable actinic light source, such as a 200-watt medium or high pressure mercury arc lamp.
- a suitable actinic light source such as a 200-watt medium or high pressure mercury arc lamp.
- the exposure time and incident industry will be determined empirically to obtain optimum results with a given mask and photoresist, but generally an exposure of about 30 to about 60 seconds with an incident intensity of from 3000 to 4600 microwatts/cm 2 will give satisfactory results.
- the photoresist is developed in an alkaline aqueous solution of an organic or inorganic base, such as an organic amine.
- the alkaline aqueous developer contains a small quantity of a surfactant to lower the surface tension thereof.
- the developer may contain from about 0.01 to about 25 percent of the base and from about 0.1 to about 0.5 percent of the surfactant, when used.
- Dialkyl- and dialkanolamines such as diethylethanolamine, diethylamine, diethanolamine, triethanolamine, etc., cyclic amines, such as piperidine and the like, alkali metal salts of strong and weak acids, such as sodium hydroxide, sodium carbonate, sodium dihydrogen phosphate and the like, are quite suitable as the base.
- Useful surfactants include an alkyl aryl sulfonate or an ethylene oxide adduct of a long chain alcohol or the like.
- Development time will be determined empirically, as is customary, but usually development can be completed in about 5 to 60 seconds. Room temperature (about 20° C) is entirely suitable, but elevated temperatures can be used, if desired.
- the photoresist thus formed has excellent resistance to acid etches, and where it is to be used with acid etches at a temperature below about 200° C, the developed plate can be used as is.
- the plate is given an overall exposure to actinic light to decompose the diazide remaining on the plate, such as for 60 to 180 seconds at about 3000 microwatts/cm 2 , and the polyamic acid condensation product is converted to the polyimide form by heating the photoresist for about 30 minutes at 220° or higher.
- the polyimide form will withstand the basic etches.
- the plate is preferably given the overall exposure described above, to avoid any possibility of image distortion resulting from nitrogen gas released by thermal decomposition of the diazide at the processing temperature.
- the overall exposure step may be omitted if the photoresist is heated slowly during use to avoid rapid decomposition of the diazide.
- the conversion to the polyimide occurs during use.
- the polyamic acid condensation product may be converted to the polyimide form before use in order to insure thermal stability of the image during use of the photoresist at the elevated temperatures of about 200° C and higher.
- the photoresist can be used in any semi-conductor processing technique without thermal distortion.
- the photoresist layer can be cleanly stripped from the support by treatment with a strong acid, such as sulfuric acid, at elevated temperature, such as 140° to 180° C, for a few minutes.
- a photoresist composition was prepared by admixing:
- photoresists were prepared by spin coating the resulting admixture for 60 seconds on a glass support at the speeds noted in Table I to obtain coatings of different thicknesses.
- a precoat of hexamethyldisilazane was used, but other silazanes can be used, as is customary.
- the solvent was removed after spin coating by heating the plates at 80° C for one hour.
- photoresists were prepared having a coating of 1.2 ⁇ of the photoresist composition on glass plates.
- the photoresists were then given a UV exposure through a split field high resolution test mask with a 200 watt medium pressure mercury arc source.
- the incident intensity was of the order of 3,000 microwatts/cm 2 and an exposure time of 60 seconds was found to be adequate.
- the photoresist plates were given an overall UV exposure using the same lamp and incident intensity as in the imaging exposure for exposure times of 60 and 120 seconds in order to photodecompose the quinone diazide.
- the plates thus prepared were heated at 300° C for 1 hour, and no image distortion was noted even at the 1 micron geometry.
- This Example shows that the photoresist herein disclosed is particularly useful for the etching of aluminum layers, which requires vigorous acidic etching solutions employed at elevated temperature, about 60° C, to shorten the time expended in etching. Many commercial positive resists cannot withstand the combination of highly active acid etches and high temperature, whereas the present resist can while providing good resolution and fidelity of etched images.
- a glass plate coated by vapor phase deposition with 10,000A of pure aluminum was coated with the photoresist composition of Example 1 by spinning at 2500 rpm for 60 seconds to yield a thickness of 1.0 ⁇ .
- the plate was then baked (prebake) at 80° C. After cooling, the plate was exposed in contact with a high resolution mask with both dark field and clear field features, the smallest of which were 1.25 ⁇ , by means of a UV light source of intensity of 3000 ⁇ watts/cm 2 for 60 seconds.
- the exposed plate was then developed by immersion in 0.5% aqueous solution of diethylethanolamine for 15 seconds at 22° C followed by rinsing in deionized water.
- the plate was then given an overall (non-imagewise) exposure for 60 seconds using the same UV light source, and then post-baked for 15 minutes at 200° C. After allowing the plate to cool, it was immersed in the following etch solution for 2 minutes at 60° C:
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/597,226 US4093461A (en) | 1975-07-18 | 1975-07-18 | Positive working thermally stable photoresist composition, article and method of using |
CA250,802A CA1063416A (en) | 1975-07-18 | 1976-04-22 | Photoresist composition containing orthoquinone or naphthoquinone diazide and polyamic acid condensation product |
IT23187/76A IT1060035B (it) | 1975-07-18 | 1976-05-12 | Sostanza protettiva fotosensibile termostabile di tipo positivo |
GB19875/76A GB1548583A (en) | 1975-07-18 | 1976-05-13 | Photoresist |
FR7615556A FR2317680B1 (fr) | 1975-07-18 | 1976-05-21 | Photo-reserves thermiquement stables et positives |
CH874876A CH619055A5 (de) | 1975-07-18 | 1976-07-08 | |
DE19762631535 DE2631535A1 (de) | 1975-07-18 | 1976-07-14 | Positiv arbeitendes, waermebestaendiges fotoresist |
JP51083611A JPS5213315A (en) | 1975-07-18 | 1976-07-15 | Photoresist composition |
NL7607897.A NL164975C (nl) | 1975-07-18 | 1976-07-16 | Werkwijze voor de bereiding van positief werkende lichtgevoelige samenstelling, werkwijze voor de vervaar- diging van een lichtgevoelig materiaal onder toepassing van zo'n samenstelling, gevormd voorwerp, verkregen met die werkwijze en werkwijze voor het maken van een tegen hoge temperatuur bestand fotoresistbeeld. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/597,226 US4093461A (en) | 1975-07-18 | 1975-07-18 | Positive working thermally stable photoresist composition, article and method of using |
Publications (1)
Publication Number | Publication Date |
---|---|
US4093461A true US4093461A (en) | 1978-06-06 |
Family
ID=24390630
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US05/597,226 Expired - Lifetime US4093461A (en) | 1975-07-18 | 1975-07-18 | Positive working thermally stable photoresist composition, article and method of using |
Country Status (9)
Country | Link |
---|---|
US (1) | US4093461A (de) |
JP (1) | JPS5213315A (de) |
CA (1) | CA1063416A (de) |
CH (1) | CH619055A5 (de) |
DE (1) | DE2631535A1 (de) |
FR (1) | FR2317680B1 (de) |
GB (1) | GB1548583A (de) |
IT (1) | IT1060035B (de) |
NL (1) | NL164975C (de) |
Cited By (49)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4180404A (en) * | 1977-11-17 | 1979-12-25 | Asahi Kasei Kogyo Kabushiki Kaisha | Heat resistant photoresist composition and process for preparing the same |
US4208477A (en) * | 1977-12-26 | 1980-06-17 | Asahi Kasei Kogyo Kabushiki Kaisha | Heat resistant photoresist composition and process for preparing the same |
US4268602A (en) * | 1978-12-05 | 1981-05-19 | Toray Industries, Ltd. | Photosensitive O-quinone diazide containing composition |
US4284706A (en) * | 1979-12-03 | 1981-08-18 | International Business Machines Corporation | Lithographic resist composition for a lift-off process |
US4289573A (en) * | 1979-03-30 | 1981-09-15 | International Business Machines Corporation | Process for forming microcircuits |
US4292384A (en) * | 1977-09-30 | 1981-09-29 | Horizons Research Incorporated | Gaseous plasma developing and etching process employing low voltage DC generation |
US4326018A (en) * | 1977-12-12 | 1982-04-20 | Polychrome Corporation | Lithographic printing plate |
US4329419A (en) * | 1980-09-03 | 1982-05-11 | E. I. Du Pont De Nemours And Company | Polymeric heat resistant photopolymerizable composition for semiconductors and capacitors |
US4339522A (en) * | 1979-06-18 | 1982-07-13 | International Business Machines Corporation | Ultra-violet lithographic resist composition and process |
US4339521A (en) * | 1979-08-01 | 1982-07-13 | Siemens Aktiengesellschaft | Heat resistant positive resists containing polyoxazoles |
US4369247A (en) * | 1980-09-03 | 1983-01-18 | E. I. Du Pont De Nemours And Company | Process of producing relief structures using polyamide ester resins |
US4410612A (en) * | 1980-09-03 | 1983-10-18 | E. I. Du Pont De Nemours And Company | Electrical device formed from polymeric heat resistant photopolymerizable composition |
US4414312A (en) * | 1980-09-03 | 1983-11-08 | E. I. Du Pont De Nemours & Co. | Photopolymerizable polyamide ester resin compositions containing an oxygen scavenger |
US4439516A (en) * | 1982-03-15 | 1984-03-27 | Shipley Company Inc. | High temperature positive diazo photoresist processing using polyvinyl phenol |
US4476216A (en) * | 1981-08-03 | 1984-10-09 | Amdahl Corporation | Method for high resolution lithography |
US4487827A (en) * | 1981-03-19 | 1984-12-11 | Hoechst Aktiengesellschaft | Process for the burning-in of light-sensitive layers during the preparation of printing forms |
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JPS5622428A (en) * | 1979-08-01 | 1981-03-03 | Toray Ind Inc | Polyimide pattern forming method |
JPS59100135A (ja) * | 1982-11-30 | 1984-06-09 | Japan Synthetic Rubber Co Ltd | 樹脂組成物 |
JPH0721642B2 (ja) * | 1986-06-19 | 1995-03-08 | 宇部興産株式会社 | 感光性ポリイミドのパタ−ン形成方法 |
JPH0644154B2 (ja) * | 1986-07-03 | 1994-06-08 | 宇部興産株式会社 | 有機溶媒可溶性のポジ型感光性ポリイミド組成物 |
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JP2022175020A (ja) | 2021-05-12 | 2022-11-25 | 東京応化工業株式会社 | 感光性樹脂、ネガ型感光性樹脂組成物、パターン化された硬化膜の製造方法及びカルボキシ基含有樹脂 |
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US4292384A (en) * | 1977-09-30 | 1981-09-29 | Horizons Research Incorporated | Gaseous plasma developing and etching process employing low voltage DC generation |
US4180404A (en) * | 1977-11-17 | 1979-12-25 | Asahi Kasei Kogyo Kabushiki Kaisha | Heat resistant photoresist composition and process for preparing the same |
US4310641A (en) * | 1977-11-17 | 1982-01-12 | Asahi Kasei Kogyo Kabushiki Kaisha | Heat resistant photoresist composition and process for preparing the same |
US4326018A (en) * | 1977-12-12 | 1982-04-20 | Polychrome Corporation | Lithographic printing plate |
US4316974A (en) * | 1977-12-26 | 1982-02-23 | Asahi Kasei Kogyo Kabushiki Kaisha | Polymers for use in heat resistant photoresist composition and process for preparing the same |
US4208477A (en) * | 1977-12-26 | 1980-06-17 | Asahi Kasei Kogyo Kabushiki Kaisha | Heat resistant photoresist composition and process for preparing the same |
US4268602A (en) * | 1978-12-05 | 1981-05-19 | Toray Industries, Ltd. | Photosensitive O-quinone diazide containing composition |
US4289573A (en) * | 1979-03-30 | 1981-09-15 | International Business Machines Corporation | Process for forming microcircuits |
US4339522A (en) * | 1979-06-18 | 1982-07-13 | International Business Machines Corporation | Ultra-violet lithographic resist composition and process |
US4339521A (en) * | 1979-08-01 | 1982-07-13 | Siemens Aktiengesellschaft | Heat resistant positive resists containing polyoxazoles |
US4395482A (en) * | 1979-08-01 | 1983-07-26 | Siemens Aktiengesellschaft | Method for the preparation of heat-resistant relief structures using positive resists |
US4284706A (en) * | 1979-12-03 | 1981-08-18 | International Business Machines Corporation | Lithographic resist composition for a lift-off process |
US4329419A (en) * | 1980-09-03 | 1982-05-11 | E. I. Du Pont De Nemours And Company | Polymeric heat resistant photopolymerizable composition for semiconductors and capacitors |
US4369247A (en) * | 1980-09-03 | 1983-01-18 | E. I. Du Pont De Nemours And Company | Process of producing relief structures using polyamide ester resins |
US4410612A (en) * | 1980-09-03 | 1983-10-18 | E. I. Du Pont De Nemours And Company | Electrical device formed from polymeric heat resistant photopolymerizable composition |
US4414312A (en) * | 1980-09-03 | 1983-11-08 | E. I. Du Pont De Nemours & Co. | Photopolymerizable polyamide ester resin compositions containing an oxygen scavenger |
US4487827A (en) * | 1981-03-19 | 1984-12-11 | Hoechst Aktiengesellschaft | Process for the burning-in of light-sensitive layers during the preparation of printing forms |
US4565767A (en) * | 1981-04-13 | 1986-01-21 | Hitachi, Ltd | Light-sensitive polymer composition with poly(amic acid), bisazide, and tertiary amine compound |
US4476216A (en) * | 1981-08-03 | 1984-10-09 | Amdahl Corporation | Method for high resolution lithography |
US4439516A (en) * | 1982-03-15 | 1984-03-27 | Shipley Company Inc. | High temperature positive diazo photoresist processing using polyvinyl phenol |
US4547455A (en) * | 1982-06-22 | 1985-10-15 | Toray Industries, Inc. | Process of forming polyimide pattern and developer therefor |
US5059513A (en) * | 1983-11-01 | 1991-10-22 | Hoechst Celanese Corporation | Photochemical image process of positive photoresist element with maleimide copolymer |
US4857435A (en) * | 1983-11-01 | 1989-08-15 | Hoechst Celanese Corporation | Positive photoresist thermally stable compositions and elements having deep UV response with maleimide copolymer |
US4690886A (en) * | 1984-02-14 | 1987-09-01 | Fuji Photo Film Co., Ltd. | Method for making negative working O-quinone diazide containing dry planographic printing plate utilizing multiply light exposure, development and basic treatment |
EP0194470A2 (de) * | 1985-03-11 | 1986-09-17 | International Business Machines Corporation | Verfahren und Zusammensetzung zur Resolutionsverbesserung für Mikroelektronenschaltungen |
US4745045A (en) * | 1985-03-11 | 1988-05-17 | International Business Machines Corporation | Method for improving resolution in microelectronic circuits using photoresist overlayer by using thermally processed polyimide underlayer formed from positive photoresist and polyamic acid |
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US5344748A (en) * | 1986-01-13 | 1994-09-06 | Rohm And Haas Company | Microplastic structure and method of manufacture |
US4720445A (en) * | 1986-02-18 | 1988-01-19 | Allied Corporation | Copolymers from maleimide and aliphatic vinyl ethers and esters used in positive photoresist |
US5021320A (en) * | 1986-10-02 | 1991-06-04 | Hoechst Celanese Corporation | Polyamide containing the hexafluoroisopropylidene group with O-quinone diazide in positive working photoresist |
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US4849051A (en) * | 1987-05-18 | 1989-07-18 | Siemens Aktiengesellschaft | Heat resistant positive resists and method for preparing heat-resistant relief structures |
US5037720A (en) * | 1987-07-21 | 1991-08-06 | Hoechst Celanese Corporation | Hydroxylated aromatic polyamide polymer containing bound naphthoquinone diazide photosensitizer, method of making and use |
US5106718A (en) * | 1988-10-20 | 1992-04-21 | Ciba-Geigy Corporation | Positive photoresist composition containing alkali-soluble phenolic resin, photosensitive quinonediazide compound and sulfonyl containing compound |
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US10139728B2 (en) * | 2014-01-13 | 2018-11-27 | Applied Materials, Inc. | Method for microwave processing of photosensitive polyimides |
CN111013967A (zh) * | 2014-01-13 | 2020-04-17 | 应用材料公司 | 用于光敏聚酰亚胺的微波处理的方法 |
Also Published As
Publication number | Publication date |
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FR2317680A1 (fr) | 1977-02-04 |
NL164975B (nl) | 1980-09-15 |
NL7607897A (nl) | 1977-01-20 |
NL164975C (nl) | 1981-02-16 |
CA1063416A (en) | 1979-10-02 |
JPS5213315A (en) | 1977-02-01 |
CH619055A5 (de) | 1980-08-29 |
GB1548583A (en) | 1979-07-18 |
IT1060035B (it) | 1982-07-10 |
FR2317680B1 (fr) | 1981-08-07 |
DE2631535A1 (de) | 1977-02-03 |
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